偶联尿苷二磷酸循环体系的天然产物体外糖基化修饰

doi:10.16085/j.issn.1000-6613.2019-0607

摘要/Abstract

摘要：

糖基化是天然产物的一种重要基团修饰，主要通过尿苷二磷酸(UDP)-糖基转移酶催化实现，而UDP-糖基供体价格昂贵限制了其应用，构建UDP-糖基供体再生系统可以有效解决该问题。本文从天然产物的体外糖基化修饰入手，阐述了糖基化修饰对天然产物功能的调控作用，比较了目前的糖基化修饰方法，其中基于UDP-糖基转移酶的生物法具备了重要的产业化应用前景。接着总结了各种UDP-糖基供体的合成方式，概述了偶联蔗糖合酶或海藻糖合酶的基于UDP循环的UDP-糖基供体再生系统，重点描述了UDP循环体系在萜类、黄酮类及其他化合物体外糖基化修饰中的应用，从而高效合成具有高附加值的天然产物糖苷化合物。指出偶联蔗糖合酶和UDP-糖基转移酶的循环体系是今后天然产物糖苷化合物合成的重要方式。

关键词: 天然产物, 糖基化修饰, 糖基转移酶, 尿苷二磷酸, 循环体系

Abstract:

Glycosylation is an important modification of natural products, which is mainly catalyzed by UDP-glycosyltransferase. UDP-sugar regeneration system has been constructed in recent years to reduce the costs. This paper focused on the invitro glycosylation of natural products and explained the effect of glycosylation on the function of natural products. The current methods of glycosylation modification were discussed. The biocatalytic process based on UDP-glycosyltransferase has great industrial application potential. Then, the regeneration of UDP-sugar based on UDP recycling system mediated by sucrose synthase or trehalose synthase was described. Importantly, the UDP recycling system has been applied to the invitro glycosylation of terpenoids, flavonoids and other compounds to efficiently synthesize high value-added natural product glycoside compounds. This paper pointed out that the UDP recycling system coupled with sucrose synthase and UDP-glycosyltransferase would be an important method for the glycosylation of natural products in the future.

Key words: natural products, glycosylation modification, glycosyltransferase, UDP, cycle system

中图分类号:

Q814.9

刘潇斐,张良,冯旭东,李春. 偶联尿苷二磷酸循环体系的天然产物体外糖基化修饰[J]. 化工进展, 2020, 39(1): 329-340.

Xiaofei LIU,Liang ZHANG,Xudong FENG,Chun LI. UDP regeneration system for in vitro glycosylation modification of natural products[J]. Chemical Industry and Engineering Progress, 2020, 39(1): 329-340.

图/表 8

图1 UDP-糖的生物合成途径

图2 蔗糖合酶的催化反应

图3 多酶偶联催化的原位UDP-糖循环体系

图4 海藻糖合成酶的催化反应

图5 偶联UDP再生的原人参二醇糖基化修饰[47]

图6 偶联UDP再生的甜菊糖糖基化修饰[49]

图7 偶联UDP再生的槲皮素糖基化修饰[63]

图8 偶联UDP再生的紫檀芪糖基化修饰[66]

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